1,4-Dioxane → 7-Benzyloxy-6-methoxy-3H-quinazolin-4-one

HRID 22771

反応式

HRID 22771 の反応式
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]([O:19][CH3:20])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[Cl-].[CH3:22]N(C)C=NC=[N+](C)C.O1CCOCC1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH2:12]([O:11][C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:5])[NH:6][CH:22]=[N:1]2)=[CH:7][C:8]=1[O:19][CH3:20])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

6

反応物 4

HCID 312751,4-DioxaneHCID 517045Sodium AcetateHCID 11008255Gold's ReagentHCID 124714802-Amino-4-(benzyloxy)-5-methoxybenzamide

生成物 1

HCID 1354047187-Benzyloxy-6-methoxy-3H-quinazolin-4-one収率 83.9%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 2-amino-4-benzyloxy-5-methoxybenzamide (J. Med. Chem., 1977, 20, 146-149; 10 g), (3-dimethylamino-2-azaprop-2-en-1-ylidene)dimethylammonium chloride (Gold's reagent, 7.4 g) and dioxane (100 ml) was stirred and heated to reflux for 24 hours. Sodium acetate (3.02 g) and acetic acid (1.65 ml) were added and the reaction mixture was heated for a further 3 hours. The mixture was evaporated and water was added to the residue. The resultant solid was collected by filtration, washed with water and dried. The material was recrystallised from acetic acid to give 7-benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one (8.7 g).

後処理

  1. temperatureheated
  2. temperatureto reflux for 24 hours
  3. temperaturethe reaction mixture was heated for a further 3 hours
  4. customThe mixture was evaporated
  5. additionwater was added to the residue
  6. filtrationThe resultant solid was collected by filtration
  7. washwashed with water
  8. customdried
  9. customThe material was recrystallised from acetic acid

出典と根拠

ORDレコード
ord-39555bc4030d4ec288c88a71ba08fa7f
出典データセット
uspto-grants-2005_02
特許番号
US06849625B2

関連ノート

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